Allylamine → N-((trimethylsilyl)methyl)prop-2-en-1-amine

Temperature

70 °C

To 118 mL (1.57 mol) of allylamine warmed at 40° C. in an inert atmosphere was very slowly added 100 mL (0.72 mol) of chloromethyl trimethylsilane (approximate rate of 1 mL/min). The reaction mixture was slowly warmed to 70° C. and stirred for 24 h. The reaction mixture was cooled to 0° C. and to it was added water to break up the gel and then 300 mL of 2N NaOH solution. The reaction mixture was extracted with ether. The combined organic fractions were washed with 500 mL of sat'd NaCl solution, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by distillation (bp 80-84° C. at 100 torr) to give 75 g of the title compound.

1. temperatureThe reaction mixture was cooled to 0° C. and to it
2. extractionThe reaction mixture was extracted with ether
3. washThe combined organic fractions were washed with 500 mL of sat'd NaCl solution
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationthe filtrate was concentrated
7. distillationThe residue was purified by distillation (bp 80-84° C. at 100 torr)

ORD record

ord-ad50d6cffef848ca8e7f69f33e8c3838

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06455548B2